The broad, long-term objective of this project in synthetic organic methodology is to develop a rapid, efficient, and enantioselective means of assembling biologically relevant indolizidine and quinolizidine containing natural products. Specifically the proposed research aims to extend the rhodium catalyzed [2+2+2] cycloaddition of alkenyl isocyanates with exogenous alkynes to include functionalized, highly reactive cycloalkynes. We plan to apply the newly expanded methodology to the synthesis of complex natural products: acosmine and dasycarpumine. These diazadamantane alkaloids have been used as folk medicines for the treatment of a number of ailments including syphilis and malaria. Additionally, acosmine has been shown to be effective in the treatment of diabetes in rats by increasing insulin secretion. The reasons we have chosen to pursue the synthesis of these alkaloids are twofold. First, the diazadamantane skeleton poses unique synthetic challenges, and second, the application of our methodology to the synthesis of these compounds would highlight its utility while expanding its scope beyond its current state. Ir all, the synthesis of these compounds wou|d be of benefit to the development of new drugs that could be effective in the treatment of diabetes, syphilis, and malaria.